I could start with, “it depends”, but I will try to give you a more straightforward answer.
If you are a founder and have landed on this page, why are you even asking this?. Beyond your need to ensure that you will have onboard a few anchor/marquee/strategic investors, you are signaling that you are trying to raise money in as few conversations as possible. Alex Danco perfectly describes this game theory behavior in his post ‘VCs should play bridge‘.
A business angel perspective:
My investments are constrained by a series of considerations. They have more to do with myself and my investment philosophy than with your startup, such as:
- Staying within my investment rules. As described in previous posts, I fancy an initial allocation that allows me to be comfortable if the investment sours and goes to zero. I am also looking to have some reserve cash to follow up with additional investments, in the case of the best performing startups.
- I could commit to convertible notes with a cap (read more about this in Brad Feld and Jason Meldenson’s book on Venture Deals), but my preference is to invest in equity (SAFEs being second best)
- The Added Value that I can bring to your startup.
Let me expand on this last point. I like to view myself as something more than an ATM. As a founder, you should be conscious that “Piles of Money” come in different shapes and sizes-
Some of us favor patient capital vs. quick returns. Others don’t. I don’t have any LPs behind me and no mandate to achieve any specific profits within a defined period. I only invest ‘betting/gambling’ money that could be put 100% at risk of loss, patient capital (again, I have no accountability to anybody for the way I invest other than myself and wife)
In terms of other value, I bring my ‘other skills to the table’. I generally work pro bono on legal issues for the startups in which I invest. I have also helped them with business development, recruitment, and fundraising. Furthermore, provided that we are a good fit, I am willing to work for advisor equity, vesting over time.
Finally, I belong to some business angel networks. I could either facilitate introductions or arrange for the syndication of specific investment opportunities.
Some more interesting discussions
I think of investing as placing bets. In a few startups, it is worth doubling down. For the founders, investors are the bank. Founders exploit investor biases such as the sunk costs fallacy, FOMO, etc. Sometimes some founders have no issues telling investors that the next big client or exit opportunity is just around the corner, even thought they know it it not true.
I don’t know and have no way of knowing the future. When I place my bets, I am looking for companies with optionality (multiple futures). Nevertheless, I prefer founders focused on the next leg, i.e., following just one strategy.
Cash flow is king. Companies that can generate cash recurrently, should be preferred over long-shots. I appreciate frugal innovation, bootstrapping, and founders that have demonstrated some resilience and creativity. I haven’t yet reinvested in any founders whose startups have failed, but I could be willing to do in the right circumstances.
I don’t appreciate founders that are always pivoting, but I do look for founders with a growth mentality. I see startups as a growth experiment for product/market fit, which implies the capacity to adapt and change. By the way, I also look for these characteristics in public companies – ‘Amazon Day’ mentality as opposed to the ‘Kodak way.’
I believe that trying to identify potential winners in an industry is trying to hit the jackpot without knowing your chances at the game (blissful ignorance, known unknowns). We don’t have a clue because we can not foresee how the tech/market i.e., demand/options, will turn out. It seems as futile as trying to find the black swan, not knowing the potential payout or the probability of success. I prefer to build a resilient portfolio based on the antifragile method, to diversify, be agile and flexible.
I need to plan. Founders, please keep me informed so that I can plan ahead how to allocate my own cash flow. Founders should try to avoid surprising shareholders, whether to the upside or downside.
I believe in letting your winners run – that is why I insist on pro-rata rights, having the option to decide to follow up or double down on an investment.
In my experience, founders usually find ways to be made hold by newcomer investors or acquirers. In opposition to this situation, I am a minority investor. I have to place my trust and look for protection against the founders’ bad behaviors on the aggressiveness/greediness of the lead investors or more significant shareholders.
I am not afraid of frontier technology, but do not have the funds or knowledge to invest in deep tech.
I believe in the remix design philosophy, aka ‘nothing is 100% original’.
I have found that some of the best bets are on techs that sit at the crossroads of two different industries/problems, and offer multiple reinforcing solutions to complex problems. Rather than thinking vertical, horizontal, or chain – I prefer startups that try to identify where value is easiest captured (low hanging fruit). These founders are continuously thinking about locking in the whole ecosystem while starting with the simplest solution.
“The outside world can push you into Day 2 if you won’t or can’t embrace powerful trends quickly. If you fight them, you’re probably fighting the future. Embrace them, and you have a tailwind”.
Jeff Bezos